Joe Grover sits down with Jake Bengzten, an innovative entrepreneur and the founder of Zipper.

They discuss the multi trillion dollar health care problem, the crazy premiums, extra fees and how Jake was on a mission to solve it, using his company: Zipper.
After 92 pitches, 7 investing angels, 18 months of grinding and paying himself only 3 times, he eventually hit rock bottom.

Jake realized the healthcare problem was too big to solve and it was time to shut down Zipper.

Jake shares, “There are a lot of people who choose unhappiness over uncertainty.” What matters most now, is what you are going to do after failing.

Growing up, he was exposed to the realities of entrepreneurship by his father and grandfather, both of whom started and ran small and medium sized businesses. As a young full-time college student, Jake networked his way into an entry level sales position at an up and coming Utah fintech startup called Finicity. It was an incredible journey where he took on various roles, including that of Chief of Staff. After the company was acquired by Mastercard for just under $1 Billion, Jake started contemplating making his own entrepreneurial jump.

This led to starting Zipper Health, a healthcare fintech startup focused on lowering the cost of healthcare for individuals and families. Rising healthcare costs is a problem that is near and dear to Jake.

Jake is a husband and father to 3 kids (with one more on the way at the time this episode was filmed).Outside of professional pursuits, Jake got hooked on triathlons about 10 years ago and has competed in Ironman. He is adamant about qualifying for the Ironman World Championships in Kona, Hawaii. Jake also loves playing pickup basketball, fly fishing, and golfing.

This episode was recorded on November 8th, 2024

-Links-

For Jake Bengzten:
https://www.linkedin.com/in/jake-bengtzen-0a8ab365/

For Joe Grover:

https://www.linkedin.com/in/joelgrover/

#entrepreneurship #realfword #startups #Failure #zipper

Joe Grover sits down with the journal enthusiast, traveler, entrepreneur, and founder of Rustico Leather, Isaac Childs. In this episode, they discuss how Rustico Leather started, the challenges of parting ways with loyal employees, insights into product development, and how journaling is a therapeutic tool.

Isaac has been a serial entrepreneur and business owner for most of his life. While in college, his passion for writing and travel led him to create and build Rustico.com, a leather goods company that focused on journals and notebooks. Isaac's lifelong passion for journaling and His vast knowledge and expertise have made him a highly sought-after speaker on the effective methodologies and science behind the subject. He is a practicing yogi, breathwork practitioner, and meditation guide. Isaac can often be found traveling the world, hanging out with his kids, or fly fishing on a remote spot on the river.

This episode was recorded on September 27th, 2024

-Links-

For Isaac:

https://www.instagram.com/mindfulnessmatrix/

For Joe:

https://www.linkedin.com/in/joelgrover/

#entrepreneurship #ecommerce #businessgrowth #Journaling #leathercraft #realfword

Joe Grover sits down with serial entrepreneur, mother of four, and partnership specialist Lindsey Ivie. They discuss her journey as a leader in marketing, stories from the businesses she’s consulted, and why balance can fulfill both personal and professional commitments.

Lindsey is an expert in channel sales, partner management and ecosystem development through networking and events marketing. Lindsey identifies valuable company partnerships and creates environments where those relationships thrive in the most organic, natural and productive ways. She has established valuable relationships with tech giants like Microsoft and Cisco, as well as E Commerce focused tech brands like Klaviyo and EasyPost along with other broker partners for clients. Lindsey flips the script on boring webinars and tired networking events into compelling experiences that are engaging, lead generating powerhouses.

This episode was recorded on September 19th, 2024

-Links-
For Lindsey Ivie:
https://www.linkedin.com/in/lindseyivie/

#WorkLifeBalance #Entrepreneurship #MarketingLeaders

Chapters
00:00:00 - Navigating Entrepreneurial Setbacks and Growth
00:08:37 - Sales Strategies for Startups
00:13:39 - Building Only Brands Platform and Marketplace
00:22:39 - Balancing Work and Family Life
00:30:26 - Embracing Failure and Learning Lessons
00:40:53 - Lessons From Entrepreneurial Failures and Growth
00:44:14 - Journey of Resilience and Growth

What if failure wasn’t something to be feared, but embraced as a vital part of the entrepreneurial journey? Join us in this eye-opening episode as we sit down with Steve Arntz, a renowned entrepreneur and intrapreneur, to dissect the "Real F Word"—failure. Steve candidly shares his roller-coaster ride through the business world, from getting fired from his first job to facing monumental career decisions that shaped his path. He opens up about the mental and emotional toll of these experiences, and the often unseen sacrifices that come with entrepreneurial endeavors.

You'll be taken through Steve's pivotal career moments, such as the advice he received from Dave Grow about consulting at Bain, a tempting counteroffer to stay at Lucid, and a bold promise from Ryan Smith that underscored the lucrative allure of Qualtrics. We explore how these choices were less about missing opportunities and more about finding the perfect fit. Steve's journey eventually led him to Instructure, where he learned the profound importance of risk-taking and the real lessons that come from facing commercial challenges head-on.

We round off our conversation by redefining success beyond traditional financial metrics. Steve emphasizes that true success lies in the meaningful impact on people's lives and the invaluable lessons learned. He shares his thoughts on resilience, storytelling in leadership, and the necessity of a strong support system. This episode is packed with deep insights and real-life experiences that will resonate with anyone looking to understand the true essence of success and the indispensable role of persistence in entrepreneurship. Don’t miss out on this must-listen discussion that promises to reshape your perspective on failure and success in the business world.

What if the key to solving your remote work communication woes lies in a video messaging app? In this episode, we sit down with Josh Little, a seasoned entrepreneur, to unpack the story behind Volley, an asynchronous video messaging app designed to bridge the gaps left by tools like Slack and Zoom during the pandemic. Josh takes us through the exhilarating early days of Volley's development, from the viral response to an initial survey to the rapid prototyping that garnered early traction and significant interest from both users and investors.

The journey wasn't without its hurdles. We delve into the psychological barriers that professionals encounter with video messaging and the challenge of gaining user adoption in a high-risk, low-trust work environment. We discuss the iterative process of refining Volley's features and the stark contrast between workplace communication and more personal, low-risk environments. Despite promising signs from YouTubers and content creators, Volley faced insurmountable obstacles, prompting a pivot toward a consulting model.

Join us as we listen to Josh reflect on the emotional toll of entrepreneurial failure, sharing candid insights on the impact on his health, relationships, and investor expectations. He offers valuable lessons on resilience, the importance of perseverance, and the evolving landscape of asynchronous communication. Despite the setbacks, Josh remains optimistic and driven, believing that his best work is still ahead and determined to repay the trust of his early supporters.

This episode is sponsored by Ampleo. Ampleo offers fraction executives in finance, marketing, and HR to companies of all sizes. Visit ampleo.com to learn more.

From the high stakes of securing venture capital to the crushing reality of laying off a beloved team, Bubba Page opens up about the emotional rollercoaster of tying one's identity to the fate of a business. Kickstarting our discussion with his experience at Launch Leads followed by the ambitious yet challenging Outro, Bubba provides invaluable insights into the realities of entrepreneurial life.

The emotional toll of startup failure can be devastating, but it's also a powerful catalyst for personal growth. Bubba bravely discusses the struggles of trying to sell a business amidst repeated rejections and the ensuing battles with depression and anxiety. Through candid reflections on personal setbacks and the path to recovery, we explore how faith, physical fitness, and self-reflection became pillars of Bubba's resilience. Wrapping up our conversation, we underscore the indispensable lessons learned from failure and encourage young entrepreneurs to embrace setbacks as integral steps towards success. This episode is a poignant reminder that growth often stems from our greatest challenges.

Fail. A word we spend our whole lives running away from. The truth is that failure is the most common outcome for entrepreneurs and startups, but we rarely talk about these painful experiences with perfect candor and openness. The Real F Word podcast will explore invaluable learning and insight from the stories of failed businesses and collapses. These are the real stories rarely discussed by entrepreneurs and often hidden by investors.